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Town of Highland Holiday Rentals

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Our top choices for Town of Highland holiday rentals

A backyard with a fire pit, outdoor furniture, and a deck.

1. Retro Countryside Cabin | Cozy Upstate NY Private Retreat!

Retro Countryside Cabin | Cozy Upstate NY Private Retreat!
Eldred
9.6 out of 10, Exceptional, (5 reviews)
"The place is exactly as described. Very comfortable and had everything we needed to enjoy our stay. Private and quiet. Bed was very comfortable. Pecks market close by. Will stay again."
United States
Robert R.
The price is HK$1,142
HK$3,808 total
includes taxes & fees
12 Oct - 13 Oct
Retro Countryside Cabin | Cozy Upstate NY Private Retreat!
A living room with a fireplace, sofa, TV, and a wooden table with baskets.

2. Bright, Spotless Cottage Near Bethel Woods

Bright, Spotless Cottage Near Bethel Woods
Highland
10.0 out of 10, Exceptional, (7 reviews)
"This was the perfect place for a long weekend where we wanted to be disconnected yet still have modern amenities. Everything was great from the check in process to the place itself and the location. Looking forward to staying here again in the future!"
United States
Chloe
The price is HK$1,030
HK$2,189 total
includes taxes & fees
11 Oct - 12 Oct
Bright, Spotless Cottage Near Bethel Woods
An indoor water park with a large water slide, inflatable tubes, and lush greenery.

3. 2 Lake Cabins Pool+hottub Game Room 23acs

2 Lake Cabins Pool+hottub Game Room 23acs
2.0 star property
Highland Lake
The price is HK$2,630
HK$10,402 total
includes taxes & fees
22 Oct - 23 Oct
2 Lake Cabins Pool+hottub Game Room 23acs
A covered porch with wicker furniture and a view of a blue house in the background.

4. Sweet Old Farmhouse in a Tranquil Setting

Sweet Old Farmhouse in a Tranquil Setting
Highland Lake
10.0 out of 10, Exceptional, (4 reviews)
"The property was very easy to access and easy to navigate the area with the location. Also right across from the local yoga studio was a bonus!"
United States
Anne H.
The price is HK$1,406
HK$3,424 total
includes taxes & fees
19 Oct - 20 Oct
Sweet Old Farmhouse in a Tranquil Setting
An indoor water park with a large water slide, inflatable tubes, and tropical plants.

5. Lakefront | Sport Courts | HotTub | GameRoom

Lakefront | Sport Courts | HotTub | GameRoom
Highland Lake
10.0 out of 10, Exceptional, (33 reviews)
"We had a wonderful time and definitely would recommend!"
United States
Phillip C.
The price is HK$1,670
HK$7,720 total
includes taxes & fees
15 Oct - 16 Oct
Lakefront | Sport Courts | HotTub | GameRoom
A cabin surrounded by dense forest, with a deck and outdoor seating area.

6. Enchanting River - Waterfront A Frame Cabin

Enchanting River - Waterfront A Frame Cabin
Yulan
10.0 out of 10, Exceptional, (4 reviews)
"I can’t put into words the feel of Enchanting River front. The location is BEAUTIFUL. Being able to fall asleep to the sound of the flowing water was just heaven. John is an incredible host, and I can’t wait for my next visit! "
United States
Britney P.
The price is HK$3,076
HK$5,425 total
includes taxes & fees
27 Oct - 28 Oct
Enchanting River - Waterfront A Frame Cabin
A wooden cabin with a circular structure, a wooden bench outside, and a wooden deck.

7. Ferncrest Campground

Ferncrest Campground
3.0 star property
Greentown
9.6 out of 10, Exceptional, (27 reviews)
"Loved this campground!! Being in nature, cooking on the grill, showering outside. A great experience was had, would definitely book again."
United States
Jerelle
The price is HK$1,483
HK$1,617 total
includes taxes & fees
12 Oct - 13 Oct
Ferncrest Campground
A bedroom with a large window overlooking a forest, a bed, a plant, and a hanging coat rack.

8. The Rex Hotel

The Rex Hotel
3.5 star property
Greentown
9.4 out of 10, Exceptional, (33 reviews)
"Would recommend and certainly stay again!"
United States
Jessica
The price is HK$1,619
HK$1,764 total
includes taxes & fees
28 Oct - 29 Oct
The Rex Hotel
A window with a view of a green, leafy outdoor area, possibly a garden or park.

9. Trails Head Tiny House

Trails Head Tiny House
Rock Hill
9.0 out of 10, Wonderful, (21 reviews)
"Host was very friendly and helpful. "
United States
Michael R.
The price is HK$620
HK$1,047 total
includes taxes & fees
3 Nov - 4 Nov
Trails Head Tiny House
A room with a wooden floor, a bed, a TV, and a sign with 'CABIN RULES'.

10. Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (119 reviews)
The price is HK$953
HK$1,690 total
includes taxes & fees
12 Oct - 13 Oct
Trails Head Cabin
A bedroom with a wooden ceiling, a bed with pillows, a sofa with cushions, a wooden bench, and a television on a stand.

11. Cozy Loft Cabin high above Bashakill Wildlife Refuge

Cozy Loft Cabin high above Bashakill Wildlife Refuge
Wurtsboro
9.6 out of 10, Exceptional, (34 reviews)
"Very nice place to spend the weekend with my beautiful wife for our 23rd anniversary! Thank you very much for your hospitality!"
United States
nelu
The price is HK$1,020
HK$1,791 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Loft Cabin high above Bashakill Wildlife Refuge
A cabin with a wooden deck and a staircase leading to a second-story balcony.

12. Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods

Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods
Narrowsburg
10.0 out of 10, Exceptional, (165 reviews)
"Such a beautiful place to stay and explore with my pup!"
United States
Alison H.
The price is HK$770
HK$2,391 total
includes taxes & fees
15 Oct - 16 Oct
Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods
A cozy living room with a fireplace, a sofa, and a green accent wall.

13. Bear Haven Cozy Poconos Cabin

Bear Haven Cozy Poconos Cabin
Greentown
10.0 out of 10, Exceptional, (88 reviews)
The price is HK$1,059
HK$2,038 total
includes taxes & fees
19 Oct - 20 Oct
Bear Haven Cozy Poconos Cabin
A wooden cabin with a porch, a door, and a window.

14. Close to Trails: Studio w/ Water Views

Close to Trails: Studio w/ Water Views
3.0 star property
Westbrookville
The price is HK$1,177
HK$1,875 total
includes taxes & fees
26 Oct - 27 Oct
Close to Trails: Studio w/ Water Views
A river with rocky banks and dense forest in the background.

15. Mountaintop Property on 8 acres

Mountaintop Property on 8 acres
Honesdale
8.2 out of 10, Very good, (99 reviews)
"Beautiful property and surrounding area, host is very friendly"
United States
Liam N.
The price is HK$589
HK$1,321 total
includes taxes & fees
1 Nov - 2 Nov
Mountaintop Property on 8 acres
A house with a dock by a lake, surrounded by trees and a clear sky.

16. Lakeview Cabin Duplex

Lakeview Cabin Duplex
Lake Huntington
9.6 out of 10, Exceptional, (25 reviews)
The price is HK$1,004
HK$1,835 total
includes taxes & fees
13 Oct - 14 Oct
Lakeview Cabin Duplex
A wooden interior with a staircase, a cozy seating area, and a kitchen.

17. Cozy Cabin with Fireplace, Firepit, Close to Lake

Cozy Cabin with Fireplace, Firepit, Close to Lake
Hawley
10.0 out of 10, Exceptional, (25 reviews)
"Our stay was amazing. The house is so cozy and welcoming!"
United States
Kenzie F.
The price is HK$1,059
HK$2,472 total
includes taxes & fees
18 Oct - 19 Oct
Cozy Cabin with Fireplace, Firepit, Close to Lake
A restaurant interior with a dining table set for two, featuring a plate of food, a glass of water, and a martini glass.

18. Mountaintop Hideaway ~ Piece of Paradise - Apt

Mountaintop Hideaway ~ Piece of Paradise - Apt
Honesdale
9.0 out of 10, Wonderful, (30 reviews)
The price is HK$756
HK$1,528 total
includes taxes & fees
12 Oct - 13 Oct
Mountaintop Hideaway ~ Piece of Paradise - Apt
A dining area with a table set for two, a pizza, a bottle, and glasses, overlooking a body of water with a bridge in the distance.

19. Honesdale Escape ~ A Place to Remember.

Honesdale Escape ~ A Place to Remember.
Honesdale
8.6 out of 10, Excellent, (53 reviews)
"Great time, host was super helpful! Awesome weekend with a great comfortable place to have for homebase."
United States
Charles
The price is HK$699
HK$1,458 total
includes taxes & fees
15 Oct - 16 Oct
Honesdale Escape ~ A Place to Remember.
A wooden cabin with a porch, a door, and a window.

20. Close to Trails: Studio w/ Water Views

Close to Trails: Studio w/ Water Views
Wurtsboro
10.0 out of 10, Exceptional, (12 reviews)
"Very kind and nice owner, brand new building have everything you needed"
United States
Ayur
The price is HK$863
HK$1,909 total
includes taxes & fees
12 Oct - 13 Oct
Close to Trails: Studio w/ Water Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Town of Highland Hotel Reviews

The Bradstan Boutique Hotel

The Bradstan Boutique Hotel

10/10 Excellent
"Everything at the property was just perfect from welcoming staff at check in to a delicious complimentary breakfast. We had the signature suite and could not have been happier with everything about it. The property grounds were so beautiful."
Deborah 1-night trip
Posted 12 hours ago
The Bradstan Boutique Hotel